Tuscany / Umbria

13 days/12 nights

Maximum number of participants on tour is 14

tuscany small group tours

Tuscany Small Group Tours Overview:

The incredible beauty of Tuscany & Umbria‘s hill towns provide the backdrop for the innumerable highlights of this trip. The tour begins with three nights in Pistoia, an off-the-tourist-radar jewel.  In Florence we’ll experience extraordinary art with Michelangelo’s David, an architectural walking tour and the Uffizi museum.  Pienza, pici pasta and the landscapes of the Val d’Orcia will host us for another three nights’ stay. We’ll taste Brunello wines at Montalcino and also take in sunny Cortona, an ancient Etruscan city-state.  Due to erosion and earthquakes, we’ll have to cross a footbridge to reach the inland island town Civita di Bagnoregio.

In Umbria the Basilica of San Francesco awaits us at Assisi.  We’ll cross the impressive aqueduct/bridge in medieval car-free Spoleto.  We’ll visit magnificent Orvieto, perched on a 300 meters high cliff of tufa rock. Our two-night stay in Gubbio, another famous medieval town, will be in a former 17th century monastery. At Urbino we’ll wander the halls of the most beautiful Renaissance palace in all of Italy.

And lastly, a visit to the Piazza del Campo of Siena and gelato in the main square of 13th century San Gimignano.
Join us for the best food and wines and much, much more!

Read what our travelers say about our Tuscany small group tours!

Day 1

Arrival at Florence airport, where you will be met by your tour manager and transferred to Hotel Villa Cappugi (3 nights), located in the foothills just outside of Pistoia.

Located in northern Tuscany between Florence and Lucca, Pistoia is a little-touristed jewel of a town. Existing since before Roman times it became an independent republic during the medieval era before being annexed by Florence. Surrounded by one of the largest plant and tree nurseries in Europe, today it has a charming historic center with inviting pedestrian lanes and beautiful squares, vegetable and flower markets.

We’ll be making a late afternoon trip for a guided exploration of the historic district followed by a welcome dinner of local Tuscan specialties and wine tasting at its finest restaurant.

tuscany small group tours

Day 2

Our excursion today is to Lucca, an elegant city of art ringed by a 4 kilometer massive wall that took 150 years to build. The second largest city-state after Venice and the only major city in Tuscany to resist the might of Florence, Lucca finally succumbed to the forces of Napoleon and was ruled for a time by his sister Elisa Bonaparte and was later home to the composer Giacomo Puccini.

Morning walking tour of the city with our local guide. In the afternoon you’ll have time to walk the pedestrian path atop the walls, wander Lucca’s ancient Roman streets or browse stylish shops.

Early evening we’ll dine at a Tuscan style pizzeria in the hills above Pistoia.

tuscany small group tours

Day 3

This morning will find us in the historic district of fabulous Florence, birthplace of the Renaissance. Our first visit is to the Accademia Museum to see Michelangelo’s incomparable David. Then our local guide will take us on an historical and architectural walking tour that covers the Piazza del Duomo, Piazza della Signoria, Piazza Santa Croce, Ponte Vecchio and more.

After some free time for your own explorations, we have an afternoon appointment at the Uffizi, the most famous art museum in Italy, where you’ll find masterpieces by Botticelli, Raphael, Leonardo and Caravaggio.

Included dinner in Pistoia

tuscany small group tours

Day 4

Leaving the plains of northern Tuscany for the rolling hills of the south, our first stop is for a cappuccino inside the 13th century walled fortress of Monteriggioni, the northernmost citadel of Siena in wars against Florence.

We’ll then pass through the Crete Senesi (Siena clay hills) for a visit to the abbey of Monte Oliveto Maggiore, a Benedictine monastery set amongst forests of cypress, pine and oak. The Great Cloister features the famous cycle of frescoes depicting the life of St Benedict by Signorelli and Sodoma. Included lunch.

Then we move on to the renaissance town of Pienza, the “ideal city” constructed by Pope Pius II, overlooking the cypress-lined hills of the stunning Orcia Valley. Our lodging is Hotel Corsignano (3 nights) located just outside the town walls.

tuscany small group tours

Day 5

Brunello wines are considered among the most prestigious of Italy. We begin this morning with a tour of an unique Brunello winery run entirely by women.

Then we’ll take in the hill-town and imposing castle of Montalcino, final bastion of the the Republic of Siena, with some of the most scenic settings on our tour.

In the afternoon we’ll stop by the beautiful 9th century abbey Sant’Antimo, said to have been founded by Charlemagne.

tuscany small group tours

Day 6

Today’s first visit is to the unique medieval village of Civita di Bagnoregio in the region of Lazio, isolated by earthquakes and erosion creating an inland island of nineteen inhabitants, accessible now only on foot across a 300 meter bridge!

Spectacular Orvieto sits atop a 325 meter outcrop of volcanic tufa rock, with thousands of caves underneath the city, dug out during Etruscan, Medieval and Renaissance times. We’ll explore them on a fascinating tour of Orvieto Underground. After lunch our local guide will take us through one of Italy’s most famous Gothic cathedrals, 300 years in construction, featuring the San Brizio chapel with the wonderful frescoes of Signorelli.

tuscany small group tours

Day 7

We visit three very interesting small Umbrian villages, beginning with a guided tour of the Olive Oil Museum at Torgiano, followed by a visit to Deruta, famous for its ceramics. After time for shopping and lunch we’ll visit the smallest theater in the world, the Teatro della Concordia at Monte Castello di Vibio.

Then we head for romantic Spoleto, whose 3000 year past includes Umbrians, Romans, Goths, Lombards, Franks, emperors and popes. We’ll be staying for 2 nights at the Hotel dei Duchi located in the upper town near the ancient Roman Theater.

Included dinner at a nearby ristorante where we’ll taste the famous local pasta strangozzi.

Tuscany Small Group Tours

Day 8

There is a wealth of history to explore within Spoleto – its massive 14th century fortress, cathedral, Roman walls and medieval piazzas, the amazing aqueduct-bridge, fine museums and churches, not to mention the maze of medieval town planning.

For the last ten years Spoleto has undergone an ambitious project to become a model città senza auto, car-free city. Twenty two underground moving sidewalks, fourteen escalators and seventeen elevators transport residents and tourists directly into the heart of the city. Streets that were designed for people centuries ago have now been returned to pedestrian use only!

Spoleto is home to the Festival dei Due Mondi (Two Worlds Festival), a music and opera festival held annually since 1958.

We begin today with a guided walking tour, followed by an afternoon and evening on your own.

tuscany small group tours

Day 9

Our pilgrimage this morning is to Assisi and the incomparable Basilica di San Francesco and its brilliant cycle of frescoes on the Life of Saint Francis by Giotto. Assisi has even more to offer with its 2,000 year old Piazza del Comune, the first century B.C. Temple of Minerva, numerous churches, Duomo and 14th century fortress, the Rocca Maggiore.

In the afternoon we’ll move north to Gubbio, perhaps the best preserved of medieval Umbrian towns, laying against the slopes of Monte Ingino. We’ll be staying for two nights at the 17th century former monastery, the Park Hotel ai Cappuccini. Afternoon visit to the Palazzo dei Consoli Museum and the Roman amphitheater.

Included dinner in Gubbio

tuscany small group tours

Day 10

Today we’ll take a trip into the region of Le Marche to visit Urbino whose main attraction, besides being one of the most beautiful medieval towns in central Italy, is the enormous Palazzo Ducale of Duke Federico which now houses the National Gallery of Le Marche. Here we will spend one of the most rewarding mornings of our tour. Urbino is also home to a very beautiful cathedral and the natal house of the Renaissance painter Raphael.

Free time and lunch on your own

Returning to Gubbio we’ll ride the funivia (bird-cage lift) to the top of the mountain to enjoy the views and see the Basilica of Saint Ubaldo, whose 900 year old remains are still on display.

Evening free

tuscany small group tours

Day 11

Cortona, the oldest continuously inhabited hill town in Italy, is our first destination. After a visit to the Etruscan Museum you’ll have the morning free for a delightful exploration of winding alleys, pleasant squares, small cafés and restaurants.

After lunch we’re off to San Gimignano, a tour favorite with its many towers, lovely scenery and enjoyable evenings. We’ll be staying at the 13th century Hotel La Cisterna (two nights), set in the main square of town.

tuscany small group tours

Day 12

Our last excursion is to the enchanting Gothic city of Siena, home to one of Italy’s most beautiful squares, the Piazza del Campo and what-was-to-have-been the largest cathedral in the world (interrupted by the Black Death). Our guide will walk us through Siena’s fascinating medieval story that, in surprising ways, lives on today.

Late day free in San Gimignano prior to the farewell dinner and last gelato. Our restaurant is located in the historic center with stunning views over the valley.

tuscany small group tours

Day 13

Morning transfers to Florence airport, train station & hotels. Pisa airport on request.

tuscany small group tours

2023 Single supplements


Principal towns & villages

1-3Lucca, Florence, Pistoia
4-6Monteriggioni, Pienza, Montalcino, Civita, Orvieto
7-8Torgiano, Deruta, Vibio, Spoleto
9-10Assisi, Gubbio, Urbino
11-12Cortona, San Gimignano, Siena


  • Day 1 transfer from Florence airport at 14:15. Pisa airport morning pickup on request.
  • Accommodations 12 nights
  • Tourist accommodation tax
  • All ground transportation Days 2-12
  • Porterage
  • All breakfasts, 6 dinners and 1 lunch, beverages included
  • All activities and admissions listed in Highlights
  • Full-time professional tour manager
  • Drop-off Florence & Pisa airports, station or hotel


  • City walking tours with local guides in
    • Lucca
    • Florence
    • Spoleto
    • Orvieto
    • Assisi
    • Siena
  • Michelangelo's David at the Accademia museum
  • Uffizi museum
  • Brunello cantina tour with wine tasting
  • The Etruscan Museum at Cortona
  • Palazzo dei Consoli Museum & funivia at Gubbio
  • Guided tour of the Palazzo Ducale/National Gallery of Le Marche at Urbino
  • Olive Oil Museum at Torgiano
  • Teatro della Concordia at Vibio
  • San Brizio chapel - Orvieto Duomo
  • Orvieto Underground
  • Siena Duomo

Getting there

Tour begins: Florence

Day 1 transfer from Florence Peretola Airport is at 14:15.  Morning transfer from Pisa on request.

Tour ends: Florence

Morning transfers available from 04:00-10:00 to Florence airport, train station and Pisa airport

How to get there: Book round trip tickets into Florence or Pisa airports

Pre tour: We recommend arriving to Florence a day or more prior to tour start. The city center/historic district is just a 10-15 minute taxi ride from the airport.

Day 1 — Pistoia, PT, Italia

Day 2 — Lucca, LU, Italia

Day 3 — Firenze, FI, Italia

Day 4 — Pienza, SI, Italia

Day 5 — Montalcino, SI, Italia

Day 6 — Orvieto, Terni, Italy

Day 6 — Civita di Bagnoregio, Bagnoregio, VT, Italia

Day 7 — Deruta Centro, Deruta, Province of Perugia, Italy

Day 8 — Spoleto, Province of Perugia, Italy

Day 9 — Assisi, Province of Perugia, Italy

Day 9 — Gubbio, Province of Perugia, Italy

Day 10 — Urbino, Urbino, Province of Pesaro and Urbino, Italy

Day 11 — Cortona, Province of Arezzo, Italy

Day 11 — Cortona, AR, Italia

Day 11 — San Gimignano, Siena, Italy

Day 12 — Siena, SI, Italia

Activity level

Most medieval towns were built as hilltop fortifications, so you will find a lot of uphill walking. Be prepared to spend a few hours a day on your feet.

This tour is not suited for anyone who has problems with knees, back, heart, obesity or those who cannot manage steps and moderate inclines. Age is not important as long as you are reasonably fit and a good walker. If you have mobility issues this is not the right tour for you. Please call us if you have questions.


  • Prices shown are per person, double occupancy, in euro.
  • The deposit is 800 euro per room.
  • Balance payments are due 70 days prior to tour start.
  • Deposits and balance payments are accepted by Visa and Master Card or by bank wire. After your deposit has been received we will send you an invoice with the due date and amount for the balance of payment. Should you fail to make final payment by the date specified on your invoice, we reserve the right to cancel your booking without refund.
  • Cancellations and refunds: in the unlikely event that we would cancel your tour, you would be entitled to a 100% refund within 2 weeks after the tour’s cancellation.

If you cancel your tour reservation:


1. are 50% refundable up until 180 days prior to tour start date.

2. are 100 % non-refundable less than 180 days prior to tour start date.

Balance payments

3. are 98% refundable 70 days or more prior to tour start date.

4. are 48% refundable 70 to 31 days prior to tour start date.

5. 30 days or less prior to tour start date: no refund.

Physician documented emergency medical reasons or police documented cases of accident, flood, fire or crime are required for refunds.

We do not provide refunds for: non-medical personal problems; air carrier delays or cancellations; inability to obtain passports; business problems or emergencies; etc.


Covid-19 Policy:  All tour members including tour managers and drivers must be fully vaccinated.

We recommend that you purchase a travel protection plan to help protect you and your travel investment against the unexpected. Travel protection plans can include coverage for Trip Cancellation, Trip Interruption, Emergency Medical and Emergency Evacuation/Repatriation, Trip Delay, Baggage Delay and more.

For information on available plans or to enroll, go to insuremytrip.com 

It is not possible for Amber Road Tours to provide protection coverage of any sort and you agree to buy insurance or travel at your own risk.


Transfers from Florence Airport on Day 1 (available only at scheduled time). Morning transfer from Pisa airport to Florence airport available upon request. All ground transportation Days 2 to 13, including tour manager and drivers. Morning transfers on Day 13 from San Gimignano to Florence airport, train station or hotel. 12 nights hotel accommodations with breakfast. 6 dinners and 2 lunches including beverages (wine or beer or soft drinks and water). Admissions to all sites visited as a group, as listed in the Highlights of the tour itinerary.


Air transportation, all meals not listed above, room service, phone calls, etc.

5. Arrivals

The transfers from Florence Peretola airport to our first hotel destination will be at 2 pm. For all other arrival times: the hotel is located 4 km. outside of Pistoia. It is about 35 minutes by taxi from the Florence airport or 50 minutes by train and taxi from the Florence train station. Upon request we will send you detailed arrival instructions.


You are allowed one suitcase and one carry-on bag. If you exceed this limit there may not be space in the coach to transport your excess luggage and it will be at your own expense to have it transported throughout the tour. We suggest that you bring a daypack for carrying water, guide books, jacket, rain gear, etc.

Porterage for one bag per person is included, your carry-on bag is yours to wheel or carry.


Most medieval towns were built as hilltop fortifications, so you will find a lot of uphill walking. Be prepared to spend a few hours a day on your feet. This tour is not suited for anyone who has problems with knees, back, heart, obesity or those who cannot manage steps and moderate inclines. Age is not important as long as you are reasonably fit and a good walker. If you have any difficulty walking this is not the right tour for you.


Days 1 – 11 by air-conditioned coach

Days 12 & 13 air-conditioned maxi-van taxi


Are located in quiet locations within historic districts or a short distance outside the city walls. European hotel rooms are generally smaller than those in the U.S., and have one queen bed or two single beds, with private bath.


We have space available for one or two singles on each of our tours. They are provided with single-use double rooms. The additional single supplement room cost can be found on the Calendar page of our website.

11. Prices

For our recommended tours and dates, as listed in our web site, are guaranteed for groups of six or more participants.

For groups with fewer than six participants, a supplemental charge may be applied when the estimated total cost of operating the tour exceeds the revenues paid.

We do not sell optional excursions or take you on shopping expeditions. Your additional expenses will be for non-included meals, moderate tipping where appropriate, and personal sightseeing or shopping.


We have a no smoking policy on all tour buses, at group meals and at all sites visited. The same policy applies to the use of cellular phones.


For the enjoyment of all our guests on tour we ask those who choose to travel with Amber Road Tours to be congenial, lighthearted and to take small issues in stride. Should you have any issues please address them to your tour manager – he or she is your Amber Road Tours’ representative during your time on tour. Once your tour is finished you will be emailed a link to our website where you can leave comments about your experiences and suggestions about how we can improve our services.


No responsibility is accepted for any loss, expense, accident, injury, or damage to any person or property due to the actions or omissions of any person, or any cause, including but not limited to acts of God, acts of terrorism, war, strikes, defects in machinery, breakdown of equipment, weather, pandemic, quarantine or other causes beyond our control.


Our Covid-19 protocols are designed to protect the health, safety and well being of our tour group members.  Should a traveler display symptoms of Covid-19 he or she must take a rapid antigen test. In the unfortunate event of a positive result they must immediately leave the tour, at their own expense.  Should there be a lag time between diagnosis and departure, client must remain in isolation and have no further contact with the group. Amber Road Tours will assist them in getting to their next destination. Spouse or travel companion must also be tested. If the result is negative, he or she may continue on tour.  

Amber Road Tours follows the protocols and regulations of the countries where we travel. In the absence of clear guidelines, CDC protocols regarding positive travelers will be used.

It is essential for tour participants to purchase Covid-19 protected travel insurance to cover eventual expenses and reimbursement for lost tour days.


Amber Road Tours reserves the right to accept, reject, or not retain any person as a tour participant whose condition or general deportment impedes the operation of the tour or, in the opinion of the tour manager, affects the rights and enjoyment of other guests. A guest not retained on tour shall have no cause for complaint or refund, and shall bear any and all extra expenses that ensue.


All information on this website is, to the best of our knowledge, correct. However, we reserve the right to make changes in accommodations, visits, and itineraries at any time should it become necessary or desirable. Delays or itinerary changes caused by strikes, bad weather, traffic, or other unforeseen circumstances are beyond our control and we are not obliged to pay guests compensation.